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Fri, Apr 17 - Thu, Apr 23
MKL
McKellar-Sipes Regional
ORD
O'Hare Intl.
$348 Roundtrip, found 4 days ago
$348
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Apr 17 from McKellar-Sipes Regional to O'Hare Intl., returning Thu, Apr 23, priced at $348 found 4 days ago
Fri, Apr 17 - Sun, Apr 19
MEM
Memphis Intl.
ORD
O'Hare Intl.
$494 Roundtrip, found 14 hours ago
$494
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Fri, Apr 17 from Memphis Intl. to O'Hare Intl., returning Sun, Apr 19, priced at $494 found 14 hours ago
Fri, Apr 17 - Sat, Apr 18
MEM
Memphis Intl.
MDW
Midway Intl.
$670 Roundtrip, found 4 days ago
$670
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Apr 17 from Memphis Intl. to Midway Intl., returning Sat, Apr 18, priced at $670 found 4 days ago
Thu, May 7 - Sun, May 10
MEM
Memphis
MDW
Chicago
$140 Roundtrip, found 6 hours ago
$140
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, May 7 from Memphis to Chicago, returning Sun, May 10, priced at $140 found 6 hours ago
Thu, May 7 - Sun, May 10
MEM
Memphis
ORD
Chicago
$180 Roundtrip, found 3 days ago
$180
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, May 7 from Memphis to Chicago, returning Sun, May 10, priced at $180 found 3 days ago
Sat, May 23 - Tue, May 26
MEM
Memphis
ORD
Chicago
$202 Roundtrip, found 3 days ago
$202
Roundtrip
found 3 days ago
Select United flight, departing Sat, May 23 from Memphis to Chicago, returning Tue, May 26, priced at $202 found 3 days ago
Sat, May 23 - Tue, May 26
MEM
Memphis
ORD
Chicago
$221 Roundtrip, found 3 days ago
$221
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, May 23 from Memphis to Chicago, returning Tue, May 26, priced at $221 found 3 days ago
Wed, May 13 - Sat, May 23
MEM
Memphis
ORD
Chicago
$222 Roundtrip, found 5 days ago
$222
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, May 13 from Memphis to Chicago, returning Sat, May 23, priced at $222 found 5 days ago
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (453 reviews)

Jun 3 - Jun 6

3 night stay

Memphis (MEM) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,331, price is now $912 per person
$912
per person
found 9 hours ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

LondonHouse Chicago, Curio Collection by Hilton
4.5-star property

LondonHouse Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (3,647 reviews)

Jun 5 - Jun 9

4 night stay

Memphis (MEM) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Memphis (MEM)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,340, price is now $1,415 per person
$1,415
per person
found 19 hours ago
Everything was perfect

Reviewed on Mar 9, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,427 reviews)

Jun 5 - Jun 9

4 night stay

Memphis (MEM) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Memphis (MEM)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,004, price is now $1,263 per person
$1,263
per person
found 19 hours ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.